Marketing: May 2026

Team Updates

• Casey Boone is no longer with iTrip. Jason Holden has thankfully transitioned into the role, supporting website development and technical marketing initiatives.
• Claire Monahan and Michaelean Stewart continue to lead Field Marketing efforts, working closely with Madison Harding and Jason Holden to support franchisee needs across markets.

 Website Project

• The marketing team and leadership will review the new website UX and sitemap on June 1 as part of the initial feedback round.
• The project remains on track for a full launch by the end of September.

Brand Refresh

• Brand pillars and key messaging have been reviewed with the agency, and feedback has been provided. The next review will take place the week of 6/1.
• The project remains on schedule and aligned with overall marketing and website timelines.

Franchisee Support

We have recently developed two on-site management proposals to support franchisee growth opportunities.

If you have local associations or partnerships to pursue, Marketing can assist with content review and customization for your market.

OwnerPoint Support

As you build out your 100-day campaign collateral in OwnerPoint, the Marketing team is available to review materials and provide optimization recommendations to improve performance. Reach out to your Success Manager and marketing@itrip.co for next steps.

Google Search Updates

Google continues to evolve its search experience, incorporating more AI capabilities. The intent is to keep users within its platform, reducing direct traffic to external websites. What does this mean for us?

• Optimizing your Google Business Profile is critical, as this may be the only chance for a traveler to get exposure to your business.
• This includes maintaining updated photos, accurate descriptions, and actively generating (and responding to!) reviews.
• Reach out to marketing@itrip.co for guidance and support to strengthen your local visibility.

We’re excited to welcome Casey Boone to the iTrip Marketing team as our new Web Marketing Specialist. Based in Atlanta, Casey brings extensive WordPress and SEO experience, working with brands that support NASA and AT&T. He will be leading our new website initiative. In his very first week, he’s already met with Envisionit and our internal development team to jump right into the work.

With Casey’s addition, marketing team hiring is now complete. We’re rolling out a new marketing organization structure designed to better support franchisees through more dedicated partnerships and, over time, more proactive, market-specific reporting and insights. To support this:

• Claire Monahan will partner with Jason Schnaitter’s Franchisees
• Michaelean Stewart will support Valerie Goodman’s Franchisees
• Jason Holden will support Brian and Rhonda’s Franchisees

Please continue sending all requests to marketing@itrip.co so we can track requests and collaborate effectively as a team.

Our brand refresh and website redesign initiatives are officially underway. Teams are engaged in discovery and stakeholder interviews, with a projected timeline of new brand guidelines in August and the new website launching in September. We’ll continue to share updates as milestones are reached.

Marketing is actively expanding 100‑day campaign Creative Packs in Owner Point for Franchisees using the Rentalz program. These new campaigns go beyond standard copy and are based on marketing strategies that have already proven successful in select markets. We’re also collaborating directly with Franchisees to help shape the next Creative Packs and provide many options for owner acquisition marketing.

The Marketing team has been working hard to update exciting marketing collateral and create new pieces for all aspects of Franchisee support. Browse our Look Book of creative content here and reach out to marketing@itrip.co for any content that may be useful to you in your marketing efforts. You’ll find everything from promotional items to owner acquisition pieces and guest marketing ads. If you don’t see what you’re looking for, ask us and we can add it to queue! The Look Book will be a living document where we’ll add content as it’s created.

Planning for the upcoming Summit is underway! Summit will again be at the Opal Sol in Clearwater, FL and a Save the Date will be arriving in your Inboxes in the coming week!

Happy 2026! With the marketing budget approved, the iTrip Marketing Team is entering the year in growth mode. We are adding three new positions—doubling our team in size—to expand support and resources for local markets. Alongside this growth, brand and website refresh initiatives remain actively in progress, all designed to strengthen visibility, support owner growth, and drive bookings throughout the year.

The Q1 Property Owner Newsletter is now available. This piece provides ready-to-use content for property owner communications, including updates, tips and seasonal advice for you to share with your property owners. Customize it further with your contact information to fit your local marketing and owner engagement strategy.

Looking to enhance or improve your property owner communications for 2026? The marketing team is happy to help. Email marketing@itrip.co for more assistance.

Work on the iTrip.net revitalization continues to move forward. The team is currently finalizing the Request for Proposal and plans to distribute it to a select group of agencies this month as the next step in the process. Franchisee feedback remains an important part of the effort, with ongoing collaboration through the marketing council as we move toward execution.

We’re excited to support our franchisees in key FIFA 2026 host cities with marketing initiatives designed to capture the buzz around this global event. From targeted digital campaigns to special guest outreach, our goal is to help maximize visibility, attract bookings, and showcase properties to soccer fans traveling to these areas.

This is just the beginning: we’ll be rolling out tools, creative assets, and strategic guidance throughout the year to make sure our franchises are ready to take full advantage of this once-in-four-years opportunity.

Now is the perfect time to connect with potential property owners. Many investors and second-home buyers are evaluating opportunities for the year ahead. Reaching out now can position you as their go-to short-term rental partner.

Why it matters: Early engagement helps you secure new properties before your competitors, growing your portfolio and boosting future bookings.

How to do it:

1. Highlight the benefits of STR management – Remind potential owners how full-service management can maximize their income, handle bookings, and take the stress out of property ownership.
2. Promote upcoming market opportunities – Showcase events, seasonal trends, or high-demand periods that make listing a property now especially lucrative.
3. Leverage email, social, and local channels – Send a “Plan Your Rental Success in 2026” email to leads, post owner-focused content on social, and connect with local real estate agents who may have investor clients.
4. Feature success stories – Share short case studies or testimonials from current owners who saw strong returns last year to build credibility and trust. Invite happy property owners to leave you a 5-star review on your Google Business Profile.

A proactive approach now can help you secure new owners early in the year, ensuring your portfolio—and bookings—start strong.

Looking to enhance your owner outreach messaging? Connect with marketing@itrip.co for ways we can help.

Didn't get to attend a breakout at Summit or want to listen again? Recordings are now available!

For breakouts with a presentation deck, find the accompanying deck in a recording's folder. Download the MP3 and listen from your own device:

Main stage presentations have been uploaded to the Summit section of the Support Hub:

Summit 2026 planning is already underway! Save the date now:

Nov. 10 - 12, 2026

Clearwater Beach, FL

If you didn't get a chance to share your Summit 2025 feedback, we're still eager to hear it. Please email us: marketing@itrip.co

As we kick off 2026, our team is here to support you with marketing questions, new ideas, or any resources you need to make this year a success.

Here's to a year full of opportunity, bookings, and momentum!

The iTrip Corporate Marketing Team